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CN-121986125-A - Phthalonitrile monomer and curable composition containing same

CN121986125ACN 121986125 ACN121986125 ACN 121986125ACN-121986125-A

Abstract

The phthalonitrile monomer may have the structure of formula (1) (R 2 ) n -X-(R 1 ) m (1) wherein X is a substituted or unsubstituted aryl or aryl-alkyl group, R 1 is, or R 2 is-ch=ch 2 , n is 1 to 4, and m is 1 to 4. The curable composition may comprise a polymerizable material, wherein the polymerizable material may comprise the phthalonitrile monomer of formula (1).

Inventors

  • WAN FEN
  • LIU WEIJUN

Assignees

  • 佳能株式会社

Dates

Publication Date
20260505
Application Date
20240722
Priority Date
20230929

Claims (20)

  1. 1. A phthalonitrile monomer having the structure of formula (1) (R 2 ) n -X-(R 1 ) m (1), wherein X is a substituted or unsubstituted aryl Ar or aryl-alkyl; R 1 is Or (b) ; R 2 is-ch=ch 2 ; n is 1 to 4, and m is 1 to 4.
  2. 2. The phthalonitrile monomer of claim 1, wherein-X-comprises benzyl, biphenyl, ar 1 -O-Ar 2 , or Ar 1 -CH 2 -Ar 2 .
  3. 3. The phthalonitrile monomer of claim 2, wherein the monomer comprises a structure selected from formula (2), formula (3), or formula (4): (2) Either (or) or (b) (3) Either (or) or (b) (4)。
  4. 4. A curable composition comprising a polymerizable material and an initiator, wherein The polymerizable material comprises a phthalonitrile monomer having the structure of formula (1) (R 2 ) n -X-(R 1 ) m (1), wherein X is a substituted or unsubstituted aryl or aryl-alkyl; R 1 is Or (b) ; R 2 is-ch=ch 2 ; n is 1 to 4, and m is 1 to 4.
  5. 5. The curable composition according to claim 4, wherein-X-comprises benzyl, biphenyl, diphenyl ether, ar 1 -O-Ar 2 , or Ar 1 -CH 2 -Ar 2 .
  6. 6. The curable composition according to claim 5, wherein the phthalonitrile monomer comprises a structure selected from formula (2), formula (3) or formula (4): (2) Either (or) or (b) (3) Either (or) or (b) (4)。
  7. 7. The curable composition of claim 4, wherein the amount of phthalonitrile monomer is at least 1 weight percent and no greater than 40 weight percent based on the total weight of the polymerizable material.
  8. 8. The curable composition of claim 8, wherein the amount of phthalonitrile monomer is at least 5 weight percent and no greater than 20 weight percent based on the total weight of the polymerizable material.
  9. 9. The curable composition of claim 4, wherein the polymerizable material comprises at least one second monomer that is free of phthalonitrile groups.
  10. 10. The curable composition of claim 1, wherein the second monomer comprises an aromatic multifunctional vinyl monomer.
  11. 11. The curable composition of claim 10, wherein the second monomer comprises a divinylbenzene monomer, a trivinylbenzene monomer, a divinyldiphenyl monomer, a trivinyldiphenyl monomer, a tetravinyldiphenyl monomer, a divinyldiphenyl ether monomer, a trivinyldiphenyl ether monomer, a tetravinyldiphenyl ether monomer, a divinyldiphenyl methane monomer, a trivinyldiphenyl methane monomer, a tetravinyldiphenyl methane monomer, or any combination thereof.
  12. 12. The curable composition of claim 10 wherein the amount of aromatic polyfunctional vinyl monomer is at least 50 weight percent based on the total weight of the polymerizable material.
  13. 13. The curable composition of claim 4, wherein the curable composition has a viscosity of no greater than 30 mPa-s at 23 ℃.
  14. 14. The curable composition of claim 4 wherein the amount of the polymerizable material is at least 90 wt-% based on the total weight of the curable composition.
  15. 15. The curable composition of claim 4, wherein the polymerizable material has a carbon content of at least 80% based on the total molecular weight of the polymerizable material.
  16. 16. A laminate comprising a substrate and a cured layer overlying the substrate, wherein the cured layer is formed from the curable composition of claim 4.
  17. 17. The laminate of claim 16, wherein the cured layer has an initial thermal degradation temperature T (X) of at least 400 ℃.
  18. 18. A method of forming a cured layer on a substrate, comprising: Applying a layer of a curable composition on the substrate, wherein the curable composition comprises a polymerizable material comprising a phthalonitrile monomer having the structure of formula (1) (R 2 ) n -X-(R 1 ) m (1), wherein X is a substituted or unsubstituted aryl or aryl-alkyl group; R 1 is Or (b) R 2 is-CH=CH 2 , n is 1 to 4, and m is 1 to 4; Contacting the curable composition with an imprint template or superstrate; polymerizing the curable composition with light or heat to form the cured layer, and The imprint template or superstrate is removed from the solidified layer.
  19. 19. The method of claim 18, wherein the cured layer has an initial thermal degradation temperature T (X) of at least 400 ℃.
  20. 20. A method of making an article, comprising: forming a cured layer on a substrate according to claim 18; Forming a pattern on the substrate; processing the substrate on which the pattern has been formed in the forming, and The article is manufactured from the substrate processed in the processing.

Description

Phthalonitrile monomer and curable composition containing same Technical Field The present disclosure relates to a phthalonitrile monomer and a curable composition for Inkjet Adaptive Planarization (IAP) comprising the same, wherein the curable composition is suitable for forming a cured layer having high thermal stability. Background Inkjet Adaptive Planarization (IAP) is a process of planarizing a surface of a substrate (e.g., a wafer including circuitry) by spraying droplets of a photocurable composition onto the surface of the substrate and directly contacting the planar superstrate with an added liquid to form a planar liquid layer. The flat liquid layer is typically cured under UV light or heat exposure and after removal of the superstrate a flat polymer surface is obtained which may be subjected to subsequent processing steps such as baking steps, etching steps and/or further deposition steps. The subsequent baking of the formed cured layer is typically carried out at temperatures which may reach 350 ℃ or 400 ℃ and even 450 ℃ and requires high thermal stability and low shrinkage of the photo-cured layer. Most current UV-cured resists are acrylate-based resists that begin to degrade before 300 ℃. There is a need for improved IAP materials in which the curable composition has a long shelf life and which can form a flat cured layer with high thermal stability during subsequent processing. Disclosure of Invention In one embodiment, the phthalonitrile monomer may have the structure of formula (1) (R 2)n–X–(R1)m (1), wherein X is a substituted or unsubstituted aryl (Ar) or aryl-alkyl group; R 1 is Or (b)R 2 is-ch=ch 2, n is 1 to 4, and m is 1 to 4. In one aspect, X of formula (1) of the phthalonitrile monomer may comprise benzyl, biphenyl, ar 1-O-Ar2, or Ar 1-CH2-Ar2. In particular aspects, the monomer may comprise a structure selected from formula (2), formula (3), or formula (4): (2) Either (or) or (b) (3) Either (or) or (b) (4)。 In another embodiment, the curable composition may comprise a polymerizable material, wherein the polymerizable material may comprise a phthalonitrile monomer having the structure of formula (1) (R 2)n-X-(R1)m (1) wherein X is a substituted or unsubstituted aryl or aryl-alkyl group; R 1 isOr (b)R 2 is-ch=ch 2, n is 1 to 4, and m is 1 to 4. In one aspect of the curable composition, X of formula (1) of the phthalonitrile monomer may comprise benzyl, biphenyl, diphenyl ether, ar 1-O-Ar2, or Ar 1-CH2-Ar2. In another aspect, the phthalonitrile monomer of the curable composition may have a structure selected from formula (2), formula (3) or formula (4): (2) Either (or) or (b) (3) Either (or) or (b) (4)。 In one embodiment of the curable composition, the amount of phthalonitrile monomer of formula (1) may be at least 1 wt% and not more than 40 wt%, based on the total weight of the polymerizable material. In particular aspects, the amount of phthalonitrile monomer can be at least 5 weight percent and no greater than 20 weight percent based on the total weight of the polymerizable material. In another embodiment of the curable composition, the polymerizable material may comprise at least one second monomer that is free of phthalonitrile groups. In one aspect, the at least one second monomer in the curable composition may comprise an aromatic multifunctional vinyl monomer. In particular aspects, the second monomer may comprise a divinylbenzene monomer, a trivinylbenzene monomer, a divinyldiphenyl monomer, a trivinyldiphenyl monomer, a tetravinyldiphenyl monomer, a divinyldiphenyl ether monomer, a trivinyldiphenyl ether monomer, a tetravinyldiphenyl ether monomer, a divinyldiphenyl methane monomer, a trivinyldiphenyl methane monomer, a tetravinyldiphenyl methane monomer, or any combination thereof. In another aspect of the curable composition, the amount of the aromatic multifunctional vinyl monomer of the second monomer may be at least 50 weight percent based on the total weight of the polymerizable material. In one embodiment, the curable composition may have a viscosity of no more than 30 mPa-s at 23 ℃ as measured according to Brooflield method. In another embodiment of the curable composition, the amount of polymerizable material may be at least 90 wt-% based on the total weight of the curable composition. In one aspect of the curable composition, the polymerizable material can have a carbon content of at least 80% based on the total molecular weight of the polymerizable material. In another embodiment, the laminate may include a substrate and a cured layer overlying the substrate, wherein the cured layer may be formed from the above-described curable composition. In one aspect of the laminate, the initial thermal degradation temperature T (X) of the cured layer may be at least 400 ℃. In another embodiment, a method of forming a cured layer on a substrate may include applying a layer of a curable composition to the substrate, wherein the curable composition includes a polymerizable mate